Gravity, Schmravity: What Is Falling Up?

Welcome to Falling Up, the go-to place where disasters have job descriptions and optimism comes with a minor limp.

I’m not sure whether you’re here for the schadenfreude or you just want to watch someone spectacularly misunderstand “success,” but this is where I take swings at the everyday comedy of rejection – as a writer, a seasoned cold caller, an amateur humorist & doodler, and my big-ass factory of accidental lessons I’ve learned along the way.

I made it to the top… of something.

First things first: I am distinctly stupider than Charlie Munger. But I’m pretty good at bouncing back in style. If you've ever tripped over your own resilience and ended up somewhere unexpected, you’ll feel right at home.

What to expect:

Stories of trying (and sometimes failing) where failing is the punchline.
Analysis, frameworks, and perfectly serviceable acronyms for the kind of problems people shrug about at happy hour.
Admissions of mistakes – my own, mostly, but occasionally ones borrowed from history, the news, fiction, culture, or cold calls gone awry.
Humorous digressions that start in the trenches and wind up in the clouds.
Lists, metaphors, and diagrams for the mildly obsessed.
Honest answers to rhetorical questions (including a few you didn’t think to ask).

I’m less interested in clarity than candor. I’ll take an awkward truth over a polished narrative any day.

The name Falling Up is borrowed from Shel Silverstein – a hero of mine since childhood. Shel’s book was one of my early obsessions; he wrote with the kind of gentle irreverence and sideways wisdom I still aspire to most days.

Cover of 'Falling Up' by Shel Silverstein, showing a child falling upward above cartoon houses.

His book taught me (by way of limericks, pratfalls, and illustrations of kids sprouting from sidewalks) that stumbling can look suspiciously like flying, if you really squint.

So, the name’s a tribute. Not cause I write poems about hippos in the bathtub (although I might), but if there’s a style guide for resilient joy and comic slip-ups, Shel wrote most of it.

If anything here feels like a gentle nod to him, that’s entirely intentional. :–)

Progress here rarely looks like “progress”. There are goofs, cringe-worthy confessions, and a lot of first-person humility. If you leave with more questions than you came in with, you’re doing it right.

Oh, and if satire is your vice, you might have come across me on Medium – where I’ve written pieces like:

Finally, you can find my more earnest experiments over at Vice Versa – if you’re interested in how humans, machines, and ambition collide in a feedback loop of invention and surprise, that’s another room I’m still painting. All the blueprints are half-finished, and the questions are always under revision.

Feel free to stop by, bring your digital scratch pad, and don’t mind the philosophical sawdust on the floor.

Thanks for reading. Let’s fall up together.

-Tiffany